Acetamide, N-(9,10-dihydro-9,10-dioxo-1-anthracenyl)-2-[(3-hydroxypropyl)amino]- | 889953-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Acetamide, N-(9,10-dihydro-9,10-dioxo-1-anthracenyl)-2-[(3-hydroxypropyl)amino]-
• 英文别名: N-(9,10-dioxoanthracen-1-yl)-2-(3-hydroxypropylamino)acetamide
• CAS: 889953-21-3
• 化学式: C₁₉H₁₈N₂O₄
• mdl: MFCD06617114
• 分子量: 338.363
• InChiKey: LGQSLAAFDHGHFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetamide, N-(9,10-dihydro-9,10-dioxo-1-anthracenyl)-2-[(3-hydroxypropyl)amino]- 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以68.8%的产率得到N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-2-(3-hydroxypropylamino)acetamide hydrochloride
  参考文献：
  名称：

  Novel aromatic–polyamine conjugates as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase

  摘要：

  Three types of aromatic-polyamine conjugates (6a-6s) were designed, synthesized and evaluated as potential inhibitors for cholinesterases (ChEs). The results showed that anthraquinone-polyamine conjugates (AQPCs) exhibited the most potent acetylcholinesterase (AChE) inhibitory activity with IC50 values from 1.50 to 11.13 mu M. Anthracene-polyamine conjugates (APCs) showed a surprising selectivity (from 76- to 3125-fold) and were most potent at inhibiting butyrylcholinesterase (BChE), with IC50 values from 0.016 to 0.657 mu M. A Lineweaver-Burk plot and molecular modeling studies indicated that the representative compounds, 6l and 6k, targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of ChEs. Furthermore, APCs did not affect HepG2 cell viability at the concentration of 100 mu M. Consequently, these polyamine conjugates could be thoroughly and systematically studied for the treatment of AD. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.045
• 作为产物：
  描述：

  1-aminoanthraquinone 在 吡啶 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 Acetamide, N-(9,10-dihydro-9,10-dioxo-1-anthracenyl)-2-[(3-hydroxypropyl)amino]-
  参考文献：
  名称：

  Novel aromatic–polyamine conjugates as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase

  摘要：

  Three types of aromatic-polyamine conjugates (6a-6s) were designed, synthesized and evaluated as potential inhibitors for cholinesterases (ChEs). The results showed that anthraquinone-polyamine conjugates (AQPCs) exhibited the most potent acetylcholinesterase (AChE) inhibitory activity with IC50 values from 1.50 to 11.13 mu M. Anthracene-polyamine conjugates (APCs) showed a surprising selectivity (from 76- to 3125-fold) and were most potent at inhibiting butyrylcholinesterase (BChE), with IC50 values from 0.016 to 0.657 mu M. A Lineweaver-Burk plot and molecular modeling studies indicated that the representative compounds, 6l and 6k, targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of ChEs. Furthermore, APCs did not affect HepG2 cell viability at the concentration of 100 mu M. Consequently, these polyamine conjugates could be thoroughly and systematically studied for the treatment of AD. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.045

文献信息

• Novel aromatic–polyamine conjugates as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase
  作者：Chen Hong、Wen Luo、Dong Yao、Ya-Bin Su、Xin Zhang、Run-Guo Tian、Chao-Jie Wang

  DOI：10.1016/j.bmc.2014.03.045

  日期：2014.6

  Three types of aromatic-polyamine conjugates (6a-6s) were designed, synthesized and evaluated as potential inhibitors for cholinesterases (ChEs). The results showed that anthraquinone-polyamine conjugates (AQPCs) exhibited the most potent acetylcholinesterase (AChE) inhibitory activity with IC50 values from 1.50 to 11.13 mu M. Anthracene-polyamine conjugates (APCs) showed a surprising selectivity (from 76- to 3125-fold) and were most potent at inhibiting butyrylcholinesterase (BChE), with IC50 values from 0.016 to 0.657 mu M. A Lineweaver-Burk plot and molecular modeling studies indicated that the representative compounds, 6l and 6k, targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of ChEs. Furthermore, APCs did not affect HepG2 cell viability at the concentration of 100 mu M. Consequently, these polyamine conjugates could be thoroughly and systematically studied for the treatment of AD. (C) 2014 Elsevier Ltd. All rights reserved.